The inaugural Fellows in the Imagine Pathway gathered on campus to begin a shared journey of reflection, inquiry, and purposeful exploration.
In January, the Leadership & Society Initiative had the privilege of welcoming the inaugural cohort of Fellows in the Imagine Pathway to the University of Chicago for the kick-off retreat of their fellowship year. Over four days, Fellows gathered to begin a shared journey of reflection, inquiry, and exploration.
This first retreat invited Fellows to examine their life stories and leadership trajectories alongside foundational texts spanning time and space. Together, they explored enduring questions about what it means to lead with purpose and to contribute to a flourishing society. The retreat marked the formation of a dynamic learning community committed to growth, dialogue, and generative leadership.
Each session was intentionally designed around several core learning goals: creating space for Fellows to reflect on their leadership journeys, deepening their understanding of the evolving landscape of social impact, and introducing them to the distinctive intellectual tools of the university. These goals framed a set of guiding questions that Fellows will continue to return to throughout the year such as, “what has shaped who I am and what matters most to me?” and “what is my vision for who I want to become in this next chapter?”
Through a combination of reflective inquiry and immersive engagement, Fellows explored these questions in practice. Sessions such as “Approaching Your Second Mountain” with LSI Faculty member David Brooks, and “Knowing Oneself through World Literature”, led by UChicago Professor David Wray, invited participants to use literary texts as mirrors for examining identity, values, and leadership across cultures and eras. Fellows also connected with University centers and institutes, gaining insight into the breadth of interdisciplinary scholarship and research that will inform their work throughout the fellowship.
Together, these experiences grounded the cohort in a shared intellectual and relational foundation, one that will support ongoing reflection and purposeful action in the months ahead. In their own words, Fellows reflected on what drew them to this moment and what they are beginning to discover through their time in the Imagine Pathway.
Jennifer Tescher, LSI Fellow and Founder & CEO of the Financial Health Network, reflected on the unique intellectual and collaborative environment that the fellowship provides. “I’m really looking forward to taking advantage of the wealth of professors, faculty, research materials, and centers on campus. The University offers an embarrassment of riches and that is what I’m most excited about.” She also noted the immediacy of connection forming within the cohort. “I’ve been amazed at how quickly people have gotten vulnerable with each other. One of the things I was most excited about was doing this work among peers who are navigating similar transitions, and that has not disappointed.”
For Akash Khurana, LSI Fellow and EVP for Wesco, the fellowship represents a shift in how he defines achievement and impact. “For much of my career, I have focused on growth, execution, and success. While that work has been fulfilling, I’ve reached a point where success feels less about external accomplishment and more about integrating purpose, societal impact, and humanity. That is what resonated with me when I learned about this program.” He also emphasized the importance of the fellowship’s design in allowing Fellows to pursue reflection while remaining professionally engaged. “This program provides the flexibility to continue contributing in my current role while exploring leadership from a different perspective and beginning to imagine a new chapter.”
Brian Hainline, LSI Fellow and former NCAA Chief Medical Officer, described the fellowship as both a homecoming and an invitation to step into deeper reflection. “I attended medical school at the University of Chicago and met my wife here 46 years ago. Returning now during a transition in my life feels like coming home while also searching for where I want to go next. The academic and intellectual atmosphere encourages you to pursue your dreams and challenge yourself.” He shared that one of the most meaningful aspects of the retreat has been the opportunity to pause and ask deeper questions. “So often we move quickly into doing. Here, I’ve been invited to step back and reflect not just on what I want to do, but on who I want to be. Those questions are deeply spiritual and creative. It has been both incredible and, at times, frightening in the best possible way.”
Howard Tombs, LSI Fellow, Corporate Communications Advisor and Author, highlighted the fellowship’s distinctive structure and the power of learning alongside a diverse community of accomplished peers. “This program offers the perfect blend of structure and flexibility. I’m continuing to work while preparing for a major career transition, and this experience allows me to do both thoughtfully.” He also reflected on the strength of the cohort itself. “The people selected for this program are incredibly accomplished and deeply willing to share their ideas, experiences, and time. That collective generosity is invaluable. I’m hoping this year helps me develop a broader understanding of what is possible as I consider what comes next.”
As the Fellows in the Imagine Pathway continue their journey, they carry forward not only new ideas, but also a shared commitment to purposeful action. The retreat offered an early glimpse into the possibilities that emerge when accomplished leaders pause to ask enduring questions about meaning and societal contribution.
We look forward to witnessing how this inaugural cohort continues to learn from one another, from timeless ideas, and from their own evolving aspirations as they imagine and help shape their next chapters of leadership and generativity. Learn more about the Imagine Pathway.
Fellows in the Leadership and Society Initiative Imagine Pathway returned to Hyde Park for four days of rigorous inquiry, community, and deepening clarity about the next chapters they are working to shape.
The Leadership and Society Initiative welcomes two new team members, Michelle Argento and Kelly Morgan, who will strengthen recruitment and program operations as the Initiative continues to grow and expand opportunities for leaders pursuing purpose-driven next chapters.
Fellows returned to campus for four days of rigorous inquiry, renewed connection, and deepening clarity about the motivations and intentions for future leadership.